The role of homolytic bond dissociation energy in the deprotonation of cation radicals. Examples in the NADH analogues series

Journal of the American Chemical Society

Volumn 120, Issue 12, 1998, Pages 2951-2958

  Anne, Agnès ^a   Fraoua, Sylvie ^a   Grass, Valérie ^a   Moiroux, Jacques ^a   Savéant, Jean Michel ^a  

^a UNIVERSITÉ PARIS DIDEROT   (France)

Author keywords

[No Author keywords available]

Indexed keywords

CATION; RADICAL; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE;

ARTICLE; CHEMICAL BINDING; ELECTRON TRANSPORT; MOLECULAR INTERACTION; OXIDATION; PROTON TRANSPORT;

EID: 0032053614     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja973725k     Document Type: Article

References (70)

1. (a) Bell, R. P.; Goodall, D. M. Proc. R. Soc. London, Ser. A 1966, 294, 273.
2. (b) Bordwell, F. G.; Boyle, W. J. J. Am. Chem. Soc. 1972, 94, 3907.
3. Albery, W. J.; Campbell-Crawford, A. N.; Curran, J. S. J. Chem. Soc., Perkin Trans. 1972, 2206.
4. (a) Bernasconi, C. F. Tetrahedron 1985, 41, 3219.
5. (b) Bernasconi, C. F. Acc. Chem. Res. 1987, 20, 301.
6. (c) Bernasconi, C. F. Adv. Phys. Org. Chem. 1992, 27, 119.
7. Terrier, F.; Boubaker, T.; Xiao, L.; Farrell, P. G. J. Org. Chem. 1992, 57, 3924.
8. (b) Moutiers, G.; El Fahid, B.; Goumont, R.; Chatrousse, A. P.; Terrier, F. J. Org. Chem. 1996, 61, 1978.
9. (a) Nicholas, A.; Arnold, D. R. Can. J. Chem. 1982, 60, 2165.
10. (b) Nicholas, A.; Boyd, R. J.; Arnold, D. R. Can. J. Chem. 1982, 60, 3011.
11. (a) Bordwell, F. G.; Cheng, J. P. J. Am. Chem. Soc. 1989, 111, 1792.
12. (b) Zhang, X.; Bordwell, F. G. J. Org. Chem. 1992, 57, 4163.
13. (c) Zhang, X.; Bordwell, F. G.; Bares, J. E.; Cheng, J. P. J. Org. Chem. 1993, 58, 3051.
14. (a) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Am. Chem. Soc. 1984, 106, 7472.
15. (b) Schlesener, C. J.; Amatore, C.; Kochi, J. K. J. Phys. Chem. 1986, 90, 3747.
16. (c) Masnovi, J. M.; Sankararaman, S.; Kochi, J. K. J. Am. Chem. Soc. 1989, 111, 2263.
17. (d) Sankararaman, S.; Perrier, S.; Kochi J. K. J. Am. Chem. Soc. 1989, 111, 6448.
18. (a) Bacciochi, E.; Del Giacco, T.; Elisei, F. J. Am. Chem. Soc. 1993, 115, 12290.
19. (b) Bacciochi, E.; Bietti, M.; Putignani, L.; Steenken, S. J. Am. Chem. Soc. 1996, 118, 5952.
20. (a) Dinnocenzo, J. P.; Banach, T. E. J. Am. Chem. Soc. 1989, 111, 8646.
21. (b) Dinnocenzo, J. P.; Karki, S. B.; Jones, J. P. J. Am. Chem. Soc. 1993, 115, 7111.
22. (a) Xu, W.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 1431.
23. (b) Xu, W.; Zhang, X.; Mariano, P. S. J. Am. Chem. Soc. 1991, 113, 8863.
24. (a) Reitstöen, B.; Parker, V. D. J. Am. Chem. Soc. 1990, 112, 4698.
25. (b) Parker, V. D.; Chao, Y.; Reitstöen, B. J. Am. Chem. Soc. 1991, 113, 2336.
26. (c) Parker, V. D.; Tilset, M. J. Am. Chem. Soc. 1991, 113, 8778.
27. (a) Fukuzumi, S.; Kondo, Y.; Tanaka, T. J. Chem. Soc., Perkin Trans. 2 1984, 673.
28. (b) Fukuzumi, S.; Tokuda, Y.; Kitano, T.; Okamoto T.; Otera, J. J. Am. Chem. Soc. 1993, 115, 8960.
29. Sinha, A.; Bruice, T. C. J. Am. Chem. Soc. 1984, 106, 7291.
30. (a) Tolbert, L. M.; Khanna, R. K. J. Am. Chem. Soc. 1987, 109, 3477.
31. (b) Tolbert, L. M.; Khanna, R. K.; Popp, A. E.; Gelbaum, L.; Bettomley, L. A. J. Am. Chem. Soc. 1990, 112, 2373.
32. (a) Hapiot, P.; Moiroux, J.; Savéant, J.-M. J. Am. Chem. Soc. 1990, 112, 1337.
33. (b) Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. J. Phys. Chem. 1991, 95, 2370.
34. (c) Anne, A.; Hapiot, P.; Moiroux, J.; Neta, P.; Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 4694.
35. Anne, A.; Fraoua, S.; Hapiot, P.; Moiroux, J.; Savéant, J.-M. J. Am. Chem. Soc. 1995, 117, 7412.
36. 15b (b) Happ, J. W.; Janzen, E. G.; Rudy, B. R. J. Org. Chem. 1970, 35, 3382.
37. (a) Ostovic, D.; Lee, I.-S. H.; Roberts, R. M. G.; Kreevoy, M. M. J. Org. Chem. 1985, 50, 4206.
38. (b) Anne, A.; Moiroux, J. J. Org. Chem. 1990, 55, 4608.
39. a's of the pyridiniums in acetonitrile are from ref 17b.
40. (b) Cauquis, G.; Deronzier, A.; Serve, D.; Vieil, E. J. Electroanal. Chem. 1975, 60, 205.
41. 16a,b MAHCN fits in the same correlation since the difference between the two solvents is 0.360 V.
42. (a) Parker, V. D. J. Am. Chem. Soc. 1992, 114, 7458.
43. (b) Parker, V. D. J. Am. Chem. Soc. 1993, 115, 1201 (erratum).
44. Andrieux, C. P.; Savéant, J.-M. Electrochemical Reactions. In Investigations of Rates and Mechanisms of Reactions: Bernasconi, C. F., Ed.; Wiley: New York, 1986; Vol. 6, 4/E, Part 2, pp 305-390.
45. (a) Andrieux, C. P.; Blocman, C.; Dumas-Bouchiat, J. M.; M'Halla, F.; Savéant, J.-M. J. Am. Chem. Soc. 1980, 102, 3806.
46. (b) Andrieux, C. P.; Savéant, J.-M. J. Electroanal. Chem. 1986, 205, 43.
47. (c) Andrieux, C. P.; Anne, A.; Moiroux, J.; Savéant, J.-M. J. Electroanal. 1991, 307, 17.
48. (a) Combining the data from refs 22b and 4a.
49. (b) Aue, D. H.; Bowers, M. T. Stabilities of positive ions from equilibrium gas-phase basicity measurements in Gas Phase Ion Chemistry; Bowers, M. T., Ed.; Academic Press: New York, 1969; Vol. 2, Chapter 9, p 1.
50. 23c
51. (b) Socrates, G. Infrared Characteristic Group Frequencies; Wiley: New York, 1994: p 132.
52. (c) Handbook of Chemistry and Physics, 72nd ed.; CRC Press: 1991-92; pp 9-11.
53. 24d
54. 25
55. (c) Marcus, R. A. J. Phys. Chem. A 1997, 101, 4072.
56. (d) In reality, owing to avoided crossing at the saddle point the reaction path goes through a rounded maximum, somewhat lower than the sharp discontinuous maximum shown in Figures 5b and 6b.
57. (a) Savéant, J.-M. J. Am. Chem. Soc. 1987, 109, 6788.
58. (b) Savéant, J.-M. Acc. Chem. Res. 1993, 26, 455.
59. (c) Savéant, J.-M. J. Am. Chem. Soc. 1992, 114, 10595.
60. (d) Savéant, J.-M. Dissociative Electron Transfer in Advances in Electron Transfer Chemistry; Mariano, P. S., Ed.; JAI Press: New York, 1994; Vol. 4, pp 53-116.
61. (a) Tuñón, I.; Tortonda, F. R.; Pascual-Ahuir, J. L.; Silla, E. J. Mol. Struct. (Theochem) 1996, 371, 117.
62. (b) Tortonda, F. R.; Pascual-Ahuir, J. L.; Silla, E.; Tuñón, I. J. Phys. Chem. 1995, 99, 12525.
63. (c) Tortonda, F. R.; Pascual-Ahuir, J. L.; Silla, E.; Tuñón, I. J. Phys. Chem. 1993, 97, 11087.
64. -1.
65. (a) Marcus, R. A. J. Chem. Phys. 1956, 24, 966.
66. (b) Marcus, R. A. J. Chem. Phys. 1956, 24, 979.
67. (c) Hush, N. S. J. Chem. Phys. 1958, 28, 962.
68. (d) Hush, N. S. Trans. Faraday Soc. 1961, 57, 557.
69. (e) Marcus, R. A. J. Chem. Phys. 1965, 43, 679.
70. Roberts, R. M. G.; Ostovic, D.; Kreevoy, M. M. Faraday Discuss. Chem. Soc. 1982, 74, 257.